Potassium Carbonate → HCID 68857447, compound

Participants

Reaction Conditions

Reaction Steps

To a 50 mL round bottom flask containing NMP (20 mL), methyl bromoacetate (0.35 g 2.3 mmol), and [2-(7-formyl-6-hydroxy-indazol-1-yl)-1-methyl-ethyl]-carbamic acid benzyl ester (0.751 g, 2.1 mmol) was added K2CO3 (1.4 g, 10 mmol). This mixture was heated to 90° C. for 16 h, then allowed to cool to 23° C., decanted into a saturated aqueous NaHCO3 solution (50 mL), and extracted with ethyl acetate (2×20 mL). The combined extracts were dried (Na2SO4), filtered and concentrated. The crude product was purified by chromatography (silica gel, hexanes: ethyl acetate gradient, 3:1 to 1:1) to provide an oil: LC/MS m/z 408 [M+H]+; 1H NMR (D2O): δ 8.19 (s, 1H), 8.06 (s, 1H), 7.75 (d, J=9.0 Hz, 1H), 7.43 (d, J=9.0 Hz, 1H), 7.30 (bm, 4H), 5.15 (d, 1H), 5.08 (dd, 2H), 4.8 (m, 1H), 4.6 (m, 1H), 4.29 (m, 1H), 4.01 (s, 3H), 1.19 (d, J=6.6 Hz, 3H).

Provenance & Evidence